Ethyl Acetate → HCID 44477925, compound

HRID 1805745Notes

Reaction equation

HRID 1805745 reaction equation
Br[C:2]1[C:15]2[C:16]3=[C:17]4[C:12](=[CH:13][CH:14]=2)[CH:11]=[CH:10][CH:9]=[C:8]4[CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=1.[Si:18]([O:25][CH2:26][C:27]1[CH:28]=[C:29](B(O)O)[CH:30]=[C:31]([CH2:33][O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])[CH:32]=1)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].CCOC(C)=O>C1COCC1.O.Cl[Pd]Cl>[Si:18]([O:25][CH2:26][C:27]1[CH:28]=[C:29]([C:9]2[CH:10]=[CH:11][C:12]3[C:17]4=[C:16]5[C:5](=[CH:4][CH:3]=[CH:2][C:15]5=[CH:14][CH:13]=3)[CH:6]=[CH:7][C:8]=24)[CH:30]=[C:31]([CH2:33][O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])[CH:32]=1)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 1596271-BromopyreneHCID 44204091HCID 44204091, compound

Product 1

HCID 44477925HCID 44477925, compoundYield 122.5%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 21881883Oxolane--water (1/1)Solvent2×

Procedure

0.122 g (5 mol %) of PdCl2 (dppf) was added to 0.686 g (2.44 mmol) of 1-bromopyrene in a darkroom, and dissolved with 12 ml of THF/H2O. 1.0 g (2.19 mmol) of 3,5-bis-tert-butyldimethylsilyloxymethyl Phenylboronic acid dissolved in 12 ml of THF/H2O was added, 3.66 ml (3 eq) of 2N NaOHaq was injected, the reaction was initiated in a 65° C. oil bath with light shielding, and the mixture was agitated for 24 hours. Strong fluorescence was continued with the naked eye by TLC (Hex:EtOAc=5:1). This was extracted with EtOAc, and the organic layer was washed with H2O, sat. NaHCO3 aq and sat. NaCl aq, and dried by addition of anhydrous NaSO4. The solvent was distilled off under reduced pressure to obtain 1.5203 g of a mixture of the target product and hydrolysates.

Workup

  1. additionwas added
  2. customwas initiated in a 65° C.
  3. extractionThis was extracted with EtOAc
  4. washthe organic layer was washed with H2O, sat. NaHCO3 aq and sat. NaCl aq
  5. dry with materialdried by addition of anhydrous NaSO4
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-b36cb515a1f9422f98258196c3965a8a
Source dataset
uspto-grants-2013_01
Patent number
US08354515B2

Reaction notes

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